3-(carboxymethyl)-1H-indole-2-carboxylic acid

Base Information

• Chemical Name: 3-(carboxymethyl)-1H-indole-2-carboxylic acid
• CAS No.: 31529-27-8
• Molecular Formula: C11H9NO4
• Molecular Weight: 219.197
• European Community (EC) Number: 828-747-5
• DSSTox Substance ID: DTXSID70350069
• Nikkaji Number: J377.427I
• Wikidata: Q82125806
• ChEMBL ID: CHEMBL23754
• Mol file: 31529-27-8.mol

Synonyms:3-(carboxymethyl)-1H-indole-2-carboxylic acid;31529-27-8;CHEMBL23754;2-carboxyindole-3-acetic acid;3-(carboxymethyl)indole-2-carboxylic acid;3-Carboxymethyl-1H-indole-2-carboxylic acid;Cambridge id 6772246;TimTec1_003626;Oprea1_354235;2-Carboxy-3-indoleacetic acid;SCHEMBL7463580;DTXSID70350069;CRMJDDJAUJZUDJ-UHFFFAOYSA-N;HMS1544E18;BDBM50009092;STK523968;AKOS000543316;CCG-144367;MS-0665;BB 0216496;CS-0238395;3-(carboxymethyl)-1H-indole-2-carboxylicacid;EN300-194528;F73677;AE-473/30079022;Z57697423

Chemical Property of 3-(carboxymethyl)-1H-indole-2-carboxylic acid

Chemical Property:

• Melting Point: 235-236 °C
• Boiling Point: 537.7±35.0 °C(Predicted)
• PKA: 3.54±0.30(Predicted)
• PSA: 90.39000
• Density: 1.545±0.06 g/cm3(Predicted)
• LogP: 1.49320
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 219.05315777
• Heavy Atom Count: 16
• Complexity: 304

Purity/Quality:

95% ^*data from raw suppliers

3-(carboxymethyl)-1H-indole-2-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=C(N2)C(=O)O)CC(=O)O

Technology Process of 3-(carboxymethyl)-1H-indole-2-carboxylic acid

There total 11 articles about 3-(carboxymethyl)-1H-indole-2-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

3-ethoxycarbonylmethyl-1H-indole-2-carboxylic acid ethyl ester (63158-60-1) → 2-carboxy-3-indoleacetic acid (31529-27-8)

Guidance literature:

With potassium carbonate; In methanol; water; for 16h; Reflux;

DOI:10.1055/s-0036-1588119

Reference yield: 90.0%

methyl 3-(methoxycarbonylmethyl)-1H-indole-2-carboxylate (156362-00-4) → 2-carboxy-3-indoleacetic acid (31529-27-8)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2005.05.098

Reference yield:

2-Oxoglutaric acid phenylhydrazone (17278-46-5) → 2-carboxy-3-indoleacetic acid (31529-27-8)

Guidance literature:

With formic acid; In water; for 5h; Heating;

upstream raw materials:

3-ethoxycarbonylmethyl-1H-indole-2-carboxylic acid ethyl ester

2-Oxoglutaric acid phenylhydrazone

methyl 3-(methoxycarbonylmethyl)-1H-indole-2-carboxylate

α-ketoglutaric acid

Downstream raw materials:

2-(1H-indol-3-yl)-N-benzyl acetamide

3-(benzylcarbamoyl-methyl)-indole-2-carboxylic acid

3-Methylindole

indole-3-acetic acid